Dichloromethane → 4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one

HRID 1465760Notes

Reaction equation

HRID 1465760 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:14][O:13]1.C(Cl)Cl>CO>[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C@@H:12]1[CH2:14][O:13]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 552705554-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one

Product 1

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one was resolved on a ChiralPak® AD-H column (5×25 cm) under SFC conditions on a Berger MGIII preparative SFC instrument. The racemate was diluted to 50 mg/ml in 1:1 DCM:MeOH. The separation was accomplished using 10% EtOH/CO2, flow rate 200 ml/min, 100 bar, 25° C. 500 ul Injections were spaced every 2.12 mins. The faster eluting (2R)-epoxide (I-15B) eluted at 5.2 min, and the slower eluting (2S)-epoxide (I-15A) eluted at 5.6 min.

Workup

  1. customThe separation
  2. custom10% EtOH/CO2, flow rate 200 ml/min, 100 bar, 25° C
  3. washThe faster eluting (2R)-epoxide (I-15B)
  4. washeluted at 5.2 min
  5. washthe slower eluting (2S)-epoxide (I-15A)
  6. washeluted at 5.6 min.

Sources & evidence

ORD record
ord-0533b4ad0bdd40d79c18667a96194c5d
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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